3-benzoyl-5-methyl-2,1-benzisoxazole | 136634-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-5-methyl-2,1-benzisoxazole
• 英文别名: (5-Methyl-2,1-benzoxazol-3-yl)-phenylmethanone
• CAS: 136634-27-0
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: MRLUWOGPIYJBHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-5-methyl-2,1-benzisoxazole 在 吡啶 、 乙酸酐 作用下， 反应 96.0h， 以65 mg的产率得到4H-3,1-苯并噁嗪-4-酮,6-甲基-2-苯基-
  参考文献：
  名称：

  Production of 3- benzoyl-2,1-benzisoxazoles,2-phenyl-4H-3,1-benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate

  摘要：

  A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2-phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.

  DOI：

  10.1039/p19930000511
• 作为产物：
  描述：

  4(1H)-喹啉酮,3-氯-6-甲基-2-苯基- 在 sodium hydroxide 、 sode de l'acide trichloroisocyanurique 作用下， 以 甲醇 为溶剂， 生成 3-benzoyl-5-methyl-2,1-benzisoxazole
  参考文献：
  名称：

  Production of 3- benzoyl-2,1-benzisoxazoles,2-phenyl-4H-3,1-benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate

  摘要：

  A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2-phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.

  DOI：

  10.1039/p19930000511

文献信息

• Sequential Silver‐Catalyzed Oxidative Cyclization Reactions of Unprotected 2‐Alkynylanilines to Anthranils
  作者：Antonio Arcadi、Marco Chiarini、Luana Del Vecchio、Fabio Marinelli、Véronique Michelet

  DOI：10.1002/ejoc.201601600

  日期：2017.4.26

  oxidative cyclization reactions of unprotected 2-alkynylanilines with Oxone are described. The influences of several parameters including the substrate features, oxidant, reaction conditions, and catalyst on the reaction outcome were explored. A plausible mechanism is provided for the unusual silver-catalyzed oxidative cyclization reactions of 2-alkynylanilines to anthranils.

  描述了未保护的 2-炔基苯胺与 Oxone 的原始 Ag 催化多米诺氧化环化反应的全部细节。探讨了包括底物特征、氧化剂、反应条件和催化剂在内的几个参数对反应结果的影响。为 2-炔基苯胺到邻氨基苯甲酸的不寻常的银催化氧化环化反应提供了一种合理的机制。
• Silver- versus gold-catalyzed sequential oxidative cyclization of unprotected 2-alkynylanilines with oxone
  作者：A. Arcadi、M. Chiarini、L. Del Vecchio、F. Marinelli、V. Michelet

  DOI：10.1039/c5cc08543h

  日期：——

  Divergent catalytic activity of gold and silver complexes towards domino oxidative cyclization reactions of unprotected 2-alkynylanilines.

  金和银配合物在对未保护的2-炔基苯胺进行多米诺氧化环化反应中表现出不同的催化活性。
• Novel production of 3-benzoyl-2,1-benzisoxazoles from 2-phenyl-quinolin-4(1H)-ones
  作者：Benjamin Staskun、Theodorus van Es、David G. Billing、Jan C. A. Boeyens

  DOI：10.1039/c39910000927

  日期：——

  2-Phenylquinolin-4(1H)-ones 1a and 1b react with sodium dichloroisocyanurate 2 in methanolic aqueous sodium hydroxide, to afford, after acidification, 3-benzoyl-2,1-benzisoxazoles 3a and 3b(ca. 30%).

  2-苯基喹啉-4(1H)-酮1a和1b与二氯异氰脲酸钠2在氢氧化钠甲醇水溶液中反应，酸化后得到3-苯甲酰基-2,1-苯并异恶唑3a和3b（约30%）。
• Staskun Baniamin, van Es Theodorus, J. Chem. Soc. Perkin Trans. 1, (1993) N 4, S 511- 516
  作者：Staskun Baniamin, van Es Theodorus

  DOI：——

  日期：——